31 Met Gala Beauty Moments That Made Red Carpet History

The first Monday in May is upon us, which means in a few short hours, glamorous figures from all walks of life will descend upon the Metropolitan Museum of Art for the annual Costume Institute Gala, dressed in glittering couture with magnetic hair and makeup to match.

As we pored over the most memorable beauty looks from years past in anticipation, we found a few prevailing schools of thought. First, the rule-breakers, those bold women who debuted a head-turning style on the red carpet: Dakota Johnson with a fresh chin-grazing red carpet bob, or Anne Hathaway’s shock of platinum, shaped into a faux-hawk for 2013’s punk spectacular. That year, Miley Cyrus, too, went all out with a set of gelled spikes, while eternal scene-stealer Sarah Jessica Parker had her cake and ate it, too, thanks to a sculptural black Mohawk that was, in fact, a clever headpiece.

On the other end of the beauty spectrum are those who stayed stylishly true to themselves. Sienna Miller had her golden girl moment, with a low ponytail and glowing skin to complement her sequined ensemble, while Stella McCartney and Liv Tyler appeared practically barefaced, save for a healthy flush to their cheeks. Elsewhere, Lil’ Kim brought her larger-than-life flair to the Met by matching hot pink highlights to her fur coat, and perhaps no one elevated the idea of signature individuality more than Princess Diana, who appeared every inch the British royal in 1996, from her polished bob to the sparkling diamonds and sapphires draped over her décolletage.

And then there were the wild cards—those unpredictable fashion disrupters who served up a thrilling dose of surprise or provocation. Think: Beyoncé elevating the high, sporty ponytail with an ornate crystal sheath, or Dita Von Teese and Marilyn Manson, who in 2006 brought their goth alabaster skin and twinning black manes out to play. Above, 31 iconic Met Gala beauty looks that make the case for pushing boundaries, whichever school you choose.